2276-94-0

Basic information

• Product Name: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• Synonyms: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS NO: 2276-94-0
• Molecular Formula: C₂₄H₄₀O₃
• Molecular Weight: 376.58
• Mol File: 2276-94-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 204-208 °C
• Boiling Point: 511°Cat760mmHg
• Flash Point: 276.9°C
• Appearance: /
• Density: 1.073g/cm³
• Vapor Pressure: 1.4E-12mmHg at 25°C
• Refractive Index: 1.528
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid(2276-94-0)
• EPA Substance Registry System: (4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid(2276-94-0)

Safety Data

• Hazardous Substances Data: 2276-94-0(Hazardous Substances Data)

Usage

General Description

The chemical "(4R)-4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid" is a complex organic compound that consists of a cyclopenta[a]phenanthrene core structure with side chains. It is a steroid compound that belongs to the group of corticosteroids. The compound is also known as 10,13-dimethyl-17-(1-oxopentyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol and is used in pharmacological research and in the synthesis of various pharmaceuticals.

InChI:InChI=1/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17-,18+,19-,20+,21+,23+,24-/m1/s1

Upstream product

• 81-25-4 3α,7α,12α-trihydroxy-5β-cholanic acid 
• 861-83-6 methyl chlolate 
• 1255-51-2 methyl 3β-acetyloxy-5β-cholan-24-oate 
• 81938-70-7 methyl O-mesyllithocholate 
• 104538-82-1 C₃₂H₄₆O₄ 
• 1249-75-8 methyl lithocholate 
• 434-13-9 Lithocholic acid 
• 7647-01-0 hydrogenchloride 
• 1553-56-6 dehydrolithocholic acid 
• 64-19-7 acetic acid 
• 141-52-6 sodium ethanolate 
• 106714-00-5 3β-hydroxy-5β.17βH.20ξH-cholen-(14)-oic acid-(24) 
• 91509-44-3 4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-(2,2-Dimethyl-propionyloxy)-10,13-dimethyl-7,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester 

Downstream Products

• 28083-35-4 5β.14β.17βH.20ξH-cholen-(3)-oic acid-(24) 
• 1249-75-8 methyl 3α-hydroxy-5α-cholan-24-oate 
• 434-13-9 Lithocholic acid 
• 5405-42-5 methyl 3β-hydroxy-5β-cholan-24-oate 
• 1553-56-6 dehydrolithocholic acid 
• 15074-03-0 (R)-methyl 4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 1249-75-8 3α-Hydroxy-5β-cholansaeure-methylester 
• 84573-10-4 N-(methoxycarbonylmethyl)-3-oxo-5β-cholan-24-oic acid amide 
• 1249-75-8 4-((R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 

Relevant articles and documents

Optimization of EphA2 antagonists based on a lithocholic acid core led to the identification of UniPR505, a new 3α-carbamoyloxy derivative with antiangiogenetic properties

The EphA2 receptor has been validated in animal models as new target for treating tumors depending on angiogenesis and vasculogenic mimicry. In the present work, we extended our current knowledge on structure-activity relationship (SAR) data of two related classes of antagonists of the EphA2 receptor, namely 5β-cholan-24-oic acids and 5β-cholan-24-oyl L-β-homotryptophan conjugates, with the aim to develop new antiangiogenic compounds able to efficiently prevent the formation of blood vessels. As a result of our exploration, we identified UniPR505, N-[3α-(Ethylcarbamoyl)oxy-5β-cholan-24-oyl]-L-β-homo-tryptophan (compound 14), as a submicromolar antagonist of the EphA2 receptor capable to block EphA2 phosphorylation and to inhibit neovascularization in a chorioallantoic membrane (CAM) assay.

3-MODIFIED ISO-/ISOALLO-LITHOCHOLIC ACID DERIVATIVES OR THEIR HOMO-ANALOGS FOR PREVENTING AND TREATING CLOSTRIDIOIDES DIFFICILE-ASSOCIATED DISEASES

The present invention relates to isolithocholic acid (3β-hydroxy-5β-cholan-24-oic acid) and isoallolithocholic acid (3β-hydroxy-5α-cholan-24-oic acid) together with the respective 22-homo-analogs or the deuterated analogs, which are modified in 3-position

Triplet energy management between two signaling units through cooperative rigid scaffolds

Through-bond triplet exciplex formation in donor-acceptor systems linked through a rigid bile acid scaffold has been demonstrated on the basis of kinetic evidence upon population of the triplet acceptors (naphthalene, or biphenyl) by through-bond triplet-